Polyester resin composition and a production method therefor

Patent metadata

Field	Value
Publication number	US-9388309-B2
Application number	US-201213979513-A
Country	US
Kind code	B2
Filing date	Jan 30, 2012
Priority date	Jan 31, 2011
Publication date	Jul 12, 2016
Grant date	Jul 12, 2016

Abstract

Disclosed are a copolymeric polyester resin composition having outstanding color stability (transparency) and a production method therefor. The copolymeric polyester resin composition comprises: between 95 and 99.99 percent by weight of a copolymeric polyester resin having a structure which is obtained by the copolymerization of a dicarboxylic acid component and a diol component that comprises isosorbide, and in which there is repetition of a dicarboxylic acid moiety derived from the dicarboxylic acid component and a diol moiety derived from the diol component; and between 0.01 and 5 percent by weight of an antioxidant selected from the group consisting of hindered phenol-based antioxidants, phosphite-based antioxidants, thioether-based antioxidants and mixtures thereof.

First claim

The invention claimed is:

1. A copolymerized polyester resin composition comprising:
95 to 99.99 weight % of a copolymerized polyester resin copolymerized with dicarboxylic acid components and diol components comprising isosorbide, having an alternating structure of dicarboxylic acid moieties which are derived from the dicarboxylic acid components and diol moieties which are derived from the diol components; and
0.01 to 5 weight % of an antioxidant selected from a group consisting of a hindered phenolic antioxidant, a phosphitic antioxidant, a thioetheric antioxidant and mixtures thereof;
wherein the diol components comprise 1 to 60 mol % of isosorbide and 40 to 99 mol % of 1,4-cyclohexane dimethanol, and the copolmerized polyester resin has a glass transition temperature (Tg) of 90° C. or more.

2. The copolymerized polyester resin composition according to claim 1 , wherein the dicarboxylic acid components are selected from a group consisting of aromatic dicarboxylic acid components of 8 to 20 carbon numbers, aliphatic dicarboxylic acid components of 4 to 20 carbon numbers and mixtures thereof.

3. The copolymerized polyester resin composition according to claim 1 , wherein the phosphitic antioxidant compound represented by Formula 1,

in the Formula 1, R 1 and R 2 are independently a substituted or unsubstituted alkyl group of 1 to 30 carbon atoms or a substituted or unsubstituted aryl group of 6 to 30 carbon atoms.

4. The copolymerized polyester resin composition according to claim 1 , wherein the thioetheric antioxidant is a compound represented by Formula 2 or Formula 3,

in the Formulas 2 and 3, R 3 and R 4 are independently a substituted or unsubstituted alkyl group of 1 to 30 carbon atoms or a substituted or unsubstituted aryl group of 6 to 30 carbon atoms.

5. The copolymerized polyester resin composition according to claim 1 , wherein the copolymerized polyester resin has the intrinsic viscosity of 0.15 dl/g or more at the temperature of 35° C. after dissolved with orthochlorophenol to a concentration of 1.2 g/dl in the copolymerized polyester resin.

6. A polyester resin article selected from the group consisting of a film, a sheet, a drink bottle, a baby bottle, a fiber, and an optical product which is produced with the copolymerized polyester resin composition according to claim 1 .

7. A method for preparing copolymerized polyester resin composition, comprising the steps of:
carrying out an esterification reaction or a trans-esterification reaction of dicarboxylic acid components, and diol components comprising isosorbide at the increased pressure of 0 to 10.0 kg/cm 2 and the temperature of 150 to 300° C. during an average retention time of 2 to 24 hours;
obtaining a copolymerized polyester resin composition by carrying out a polycondensation reaction for a product of the esterification reaction or the trans-esterification reaction at the reduced pressure of 400 to 0.1 mmHg and at the temperature of 150 to 300° C. during an average retention time of 1 to 24 hours; and
adding an antioxidant selected from a group consisting of a hindered phenolic antioxidant, a phosphitic antioxidant, a thioetheric antioxidant and mixtures thereof during the esterification reaction or polycondensation reaction, or mixing the antioxidant with the produced copolymerized polyester resin, for 95 to 99.99 weight % of the copolymerized polyester resin to be mixed with 0.01 to 5 weight % of the antioxidant;
wherein the diol components comprise 1 to 60 mol % of isosorbide and 40 to 99 mol % of 1,4-cyclohexane dimethanol, and the copolmerized polyester resin has a glass transition temperature (Tg) of 90° C. or more.

8. The method for preparing copolymerized polyester resin composition according to claim 7 , wherein the dicarboxylic acid components are selected from a group consisting of aromatic dicarboxylic acid components of 8 to 20 carbon numbers, aliphatic dicarboxylic acid components of 4 to 20 carbon numbers and mixtures thereof.

9. The method for preparing copolymerized polyester resin composition according to claim 7 , wherein the phosphitic antioxidant is a compound represented by Formula 1,

in the Formula 1, R 1 and R 2 are independently a substituted or unsubstituted alkyl group of 1 to 30 carbon atoms or a substituted or unsubstituted aryl group of 6 to 30 carbon atoms.

10. The method for preparing copolymerized polyester resin composition according to claim 7 , wherein the thioetheric antioxidant is a compound represented by Formula 2 or Formula 3,

in the Formulas 2 and 3, R 3 and R 4 are independently a substituted or unsubstituted alkyl group of 1 to 30 carbon atoms or a substituted or unsubstituted aryl group of 6 to 30 carbon atoms.

11. The method for preparing copolymerized polyester resin composition according to claim 7 , wherein the copolymerized polyester resin has the intrinsic viscosity of 0.15 dl/g or more at the temperature of 35° C. after dissolved with orthochlorophenol to a concentration of 1.2 g/dl in the copolymerized polyester resin.

Assignees

• Kim Dong-Jin
• Yoon Won-Jae
• Kim Jong-Ryang
• Lee Yoo-Jin
• Hwang Sin-Young
• Sk Chemicals Co Ltd

Inventors

• Kim Dong-Jin
• Yoon Won-Jae
• Kim Jong-Ryang
• Lee Yoo-Jin
• Hwang Sin-Young

Classifications

• C08G63/6926

  Dicarboxylic acids and dihydroxy compounds · CPC title

• C08K5/527

  Cyclic esters · CPC title

• Y10T428/1352

  Polymer or resin containing [i.e., natural or synthetic] · CPC title

• C08L2201/08

  Stabilised against heat, light or radiation or oxydation · CPC title

• C08K5/372

  Sulfides {, e.g. R-(S)x-R'} · CPC title